A cyclized form of L-glutamic acid
Related Products
Enantiomer(s)
31170D-Pyroglutamic Acid
Isomer(s)
36375DL-Pyroglutamic Acid
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L-Pyroglutamic Acid

Item No. 36531

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-oxo-L-proline
CAS Number
98-79-3
Synonyms
  • NSC 143034
  • (S)-5-Oxoproline
  • (–)-Pyroglutamic Acid
Molecular Formula
C5H7NO3
Formula Weight
129.1
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 16 mg/mlDMSO: 20 mg/mlEthanol: Slightly solublePBS (pH 7.2): 5 mg/ml
SMILES
O=C1CC[C@@H](C(O)=O)N1
InChi Code
InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m0/s1
InChi Key
ODHCTXKNWHHXJC-VKHMYHEASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    100 g

    $62

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    250 g

    $137

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    500 g

    $214

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    1 kg

    $365

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    Product Description

    L-Pyroglutamic acid is a cyclized form of L-glutamic acid (Item No. 30377). It is formed from L-glutamic acid or L-glutamine (Item No. 23716) by glutaminyl cyclase.1 A pyroglutamic acid-containing amyloid-β (Aβ) peptide (pGlu-Aβ (3-42)) aggregates at a higher rate than Aβ (3-42) and Aβ42 (Item No. 20574) when used at a concentration of 10 µM. It is a component of the neuropeptide adipokinetic hormone (AKH) in insects, a hormone that stimulates fatty acid oxidation during flight to provide energy.2 L-Pyroglutamic acid (500 mg/kg) increases the number of received shocks in the Vogel punished drinking task, indicating anxiolytic-like activity, in rats.3 Plasma levels of L-pyroglutamic acid are increased in patients with end-stage renal disease and pGlu-containing Aβ plaques have been found in brain tissue from patients with Alzheimer’s disease.4,5 L-Pyroglutamic acid has been used in the synthesis of fibroblast activation protein (FAP) inhibitors.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Schilling, S., Lauber, T., Schaupp, M., et al. On the seeding and oligomerization of pGlu-amyloid peptides (in vitro). Biochemistry 45(41), 12393-12399 (2006).

    2. Van der Horst, D.J. Insect adipokinetic hormones: Release and integration of flight energy metabolism. Comp. Biochem. Physiol. B Biochem. Mol. Biol. 136(2), 217-226 (2003).

    3. Beni, M., Pellegrini-Giampietro, D.E., and Moroni, F. A new endogenous anxiolytic agent: L-Pyroglutamic acid. Fundam. Clin. Pharmacol. 2(2), 77-82 (1988).

    4. Palekar, A.G., Tate, S.S., Sullivan, J.F., et al. Accumulation of 50oxo-L-proline and 5-oxo-D-proline in the blood plasma in end stage renal disease. Biochem. Med. 14(3), 339-345 (1975).

    5. Wirths, O., Bethge, T., Marcello, A., et al. Pyroglutamate Abeta pathology in APP/PS1KI mice, sporadic and familial Alzheimer’s disease cases. J. Neural Transm. (Vienna) 117(1), 85-96 (2010).

    6. Tsai, T.-Y., Yeh, T.-K., Chen, X., et al. Substituted 4-carboxymethylpyroglutamic acid diamides as potent and selective inhibitors of fibroblast activation protein. J. Med. Chem. 53(18), 6572-6583 (2010).